Dimethylformamide → HCID 18752856, compound

HRID 1173090Notes

Reaction equation

HRID 1173090 reaction equation
CN(C)C=O.[Cl:6]N1C(=O)CCC1=O.[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[NH:20][CH:19]=[CH:18]2.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[NH:20][CH:19]=[C:18]2[Cl:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 8166855-bromo-7-nitroindole

Product 1

HCID 18752856HCID 18752856, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.4 ml of dimethylformamide and 6.98 g (52.3 mmol) of N-chlorosuccinimide were added to a tetrahydrofuran solution (140 ml) containing 12.00 g (49.8 mmol) of 5-bromo-7-nitro-1H-indole, followed by stirring at room temperature overnight. An aqueous 10% sodium thiosulfate was added thereto, followed by extracting with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness, to give 14.84 g of the title compound.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was successively washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6a8a6aa338db4830ad362ab44dedd991
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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